Strain‐Promoted Cycloaddition of Cyclopropenes with o‐Quinones: A Rapid Click Reaction. Issue 32 (17th April 2018)

• Record Type: Journal Article
• Authors: Gahtory, Digvijay; Sen, Rickdeb; Kuzmyn, Andriy R.; Escorihuela, Jorge; Zuilhof, Han
• Is Part Of: Angewandte Chemie international edition. Volume 57:Issue 32(2018)
• Page Start: 10118
• Page End: 10122
• Publication Date: 2018-04-17
• Subjects: kinetics -- mass spectrometry -- metal-free click reactions -- monolayers -- polymer brushes; Chemistry -- Periodicals; 540
• DOI: 10.1002/anie.201800937
• Languages: English
• ISSNs: 1433-7851

Abstract

Abstract: Novel click reactions are of continued interest in fields as diverse as bio‐conjugation, polymer science and surface chemistry. Qualification as a proper "click" reaction requires stringent criteria, including fast kinetics and high conversion, to be met. Herein, we report a novel strain‐promoted cycloaddition between cyclopropenes and o ‐quinones in solution and on a surface. We demonstrate the "click character" of the reaction in solution and on surfaces for both monolayer and polymer brush functionalization. Abstract : Strain‐promoted reactions : Methyl‐substituted cyclopropenes have been used for conjugation with o ‐quinones in solution and on a surface. By taking advantage of the small size of cyclopropene reactants a conjugation system with fairly rapid kinetics is built.